Boras said back in October that he had received calls from 11 teams, but aside from some conflicting reports about the Mariners, we have heard very little about who might be involved in negotiations to sign Ellsbury. Many have speculated on the Cubs as a possible landing spot for the free agent center fielder, though it’s unclear whether they are actually in the mix.

Ellsbury, 30, batted .298/.355/.426 with 48 extra-base hits (nine home runs) and 53 RBI over 134 games this season while leading the majors with 52 stolen bases. Whether it happens at next week’s Winter Meetings or not, it’s safe to say that he will walk away with one of the biggest contracts this offseason.

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How can Boras avoid several conflicts of interest by representing both Elsbury and Choo? These are two guys with similar skill sets fighting for finite dollars and jobs.

What if both players want to land with the same team? Should Boras emphasize Ellsbury’s superior numbers versus lefties? Isn’t that magnifying a weakness of his other client, Choo? When one signs, won’t Boras feel pressure to get the other more dollars? Will the second one who signs for potentially less money feel that he wasn’t Boras’ top priority? Or will the first one who signs for less money feel railroaded? If Ellsbury had a different agent, would Boras emphasize Choo’s durability advantage?

They’ll likely both break the bank and, as Jules Winfield once alluded to, will be very happy. Nobody has a better track record than Boras when it comes to delivering for star players. But, if I were one of these players, I wouldn’t feel comfortable sharing an agent this offseason.

I would suggest it isn’t a conflict of interest because his own personal interests are in getting the maximum dollars for both players because that is what benefits him.

A conflict would arise in a situation where one player’s detriment benefits the other player AND the agent.

Really by signing Jacoby first to an outrageous contract it raises the value of Choo not only because he’s now the best option, but also because Jacoby’s contract (or Choo’s if he signed first for a bloated contract) establishes the market price.

One of these guys is going to get a better deal than the other. Boras hopes both numbers are as high as possible. True. But, there are some ethical nuances. The first one to sign may not be comfortable setting the market for the other- if the second player signs for much more. Don’t both players expect to get the highest numbers- in terms of dollars and years? If Choo had a different agent, wouldn’t Boras engage in some negative campaigning against him when selling Ellsbury to a GM- bad numbers against lefties, DUI, etc?

sincitybonobo - Dec 2, 2013 at 8:30 PM

And, if the second signs for less money, he might think the first was a greater priority for Boras.

I can’t imagine sharing an agent is ideal for both these guys. It does put pressure on Boras, though.

tfbuckfutter - Dec 2, 2013 at 8:33 PM

Of course one is going to get a better deal. Because one is more valuable a commodity than the other.

Frankly, they aren’t even being marketed in the same way to the same teams because they are different types of players. That’s like saying the Supermarket is involved in a conflict of interest because it sells both steak and pork and that the target market is “hungry people.”

sincitybonobo - Dec 2, 2013 at 9:05 PM

Which player is expecting less money right now? How much less? I wouldn’t want my agent balancing my interests with those of another client. I’d be curious to see what Boras has to say about this- off the record. Again, it’s financially a good problem to have to be in line for 5% of a quarter billion dollars. But would he proceed exactly the same way on behalf of both players if he were only representing one?

Not sure what kind of dollars/years he is looking for but it just seems like he has already missed a lot of games for only being age 30. If I were a GM I would approach with a great deal of caution and some real thorough medical exams in hand.

Gardner is better in Left, where he was the most valuable fielder in the league in 2010. He was so good in the field that year that he was the 5th most valuable position player in the league, despite being a slightly above average batter.

He’s not as good in CF. That said, he’s still pretty good, and his batting numbers are similar to Ellsbury. Gardner had 3 more XBH and his OPS was .022 lower. Ellsbury is more valuable, but not by a huge margin.

Perhaps more importantly, Gardner is cost-controlled and his cheap contract is year to year at this point. Both guys are the same age. One is going to be making close to $20 million next year on a 9 figure total commitment and one isn’t.

tfbuckfutter - Dec 2, 2013 at 11:25 PM

I was going to viciously mock you for this post….

I’m glad I checked the stats before doing so because you’re actually right. The difference in measurables between Gardner and Ellsbury (minus the stolen bases) doesn’t justify the difference in salary.

They are very close in career WAR too.

tfbuckfutter - Dec 2, 2013 at 11:31 PM

Of course, the biggest difference is Jacoby’s enigmatic 2011 season which no one would ever consider suggesting Gardner is capable of matching….

And which, for some reason, seems to be the suggested performance that can be expected of Ellsbury, which is ludicrous. (Oh if not for these freak injuries, that could happen to anyone because he’s not injury prone, he’d be putting up those numbers every year….it’s just bad luck. You’ll see. You’ll see.)

Kevin S. - Dec 2, 2013 at 11:43 PM

Where did this idea that Gardner isn’t fantastic in CF come from? UZR has him as a +10 CF, DRS thinks he’s a +20. Ellsbury is pretty good, but Gardner is one of the best in the game. I’d like to see the Yanks go after Ellsbury, but to play LF, not CF. His bat still profiles as plus there, given the sad state of MLB LFers these days, and his defense would be spectacularific.

riverace19 - Dec 2, 2013 at 7:59 PM

I could see something like 4 years for $60-65… Beyond that would be a reach

I am not sure where ellsbury will land, but when he is healthy he is fun to watch. The problem with him though is his health. Hopefully he has a healthy and productive few years coming up. I think if ellsbury lands with the yankees i would not mind gardner in left and ellsbury in center. Both are great defensive players so it could shake out either way. Putting ellsbury in center maximizes the value of any contract he signs as he would be seen as playing a premium defensive position, so whoever signs the check might feel more comfortable with him there. Putting ellsbury in left though may help with injury issues and may ultimately be where he ends up.

my gut says ells will be a yankee if the sox do not wake up. yanks have the need, ready cash, unlimited off field marketing potential, classy org, and will always do their best to build winners. why would ells not go there, from a pro perspective. sox had better gets serious soon or ells is gone.